Sodium Sulfite → HCID 86667431, compound

HRID 74981Notes

Reaction equation

HRID 74981 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[C:12]([Si:16]([CH3:26])([CH3:25])[O:17][C@:18]1([CH3:24])[CH2:23][CH2:22][CH2:21][CH:20]=[CH:19]1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[C:12]([Si:16]([CH3:26])([CH3:25])[O:17][C@:18]1([CH3:24])[CH2:23][CH2:22][CH2:21][C@@H:20]2[C@H:19]1[O:9]2)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 68008146(R)-tert-butyldimethyl(1-methylcyclohex-2-enyloxy)silane2×

Product 1

HCID 86667431HCID 86667431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chlorobenzenecarboperoxoic acid (2.47 g, 11.00 mmol) was added in one portion to a stirred solution of (R)-tert-butyldimethyl(1-methylcyclohex-2-enyloxy)silane, 50b, (1.98 g, 8.87 mmol) and sodium hydrogen carbonate in 30 mL of dry dichloromethane at room temperature under nitrogen. The resulting mixture was stirred for 20 hours. Then, 25% sodium sulfite solution (30 mL) was added and the resulting biphasic mixture was stirred for 15 minutes. The 2 layers were separated and the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic phases were washed with aqueous saturated NaHCO3, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by silica gel chromatography (0-10% EtOAc-hexanes gradient) to provide 647 mg of compound 50c.

Workup

  1. stirringthe resulting biphasic mixture was stirred for 15 minutes
  2. customThe 2 layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
  4. washThe combined organic phases were washed with aqueous saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel chromatography (0-10% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-c7cf6e7af4dd4d5cbbb85ac2f6d6c594
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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